There’s nothing like reminiscing about the first time you got fucked in the ass. Since I had a pretty great time and I know it can be awkward, I thought I'd share as an example how great it can be.

I started my anal journey when I was about 16 years old, almost immediately after watching a movie where a cisgender guy stops into a sperm donation clinic to raise himself some money. Essentially, he asks a nurse to help with “the donation process,” and she then proceeds to bend him over a medical table and finger his prostate until he fills the cup. Let’s just say I was mighty interested in how this whole process worked, and was all about finding out for myself.

When I started out, I was experimenting with random phallic objects and lube substitutes, like most ignorant and young folks. But when I finally got fucked in the ass properly, it all changed. My first penetrative partner was very much interested in focusing on my anal needs. They were knowledgeable about sex and were invested in making me feel comfortable and safe throughout the entire experience. For example, the first time I went to the Safe Sex Store in Ann Arbor, my partner spoke with the store owner about finding an anal toy for beginners. Also, they went ahead and asked my permission before putting my business out there, which I immensely appreciated.

We bought a silicone-based lube and a cheap (compared to what I normally buy now) dildo for the occasion. Afterward, I went back to my dorm room with my toy and lube as well as an enema kit I bought off Amazon at the time, and then went into my community-style bathroom, which if you haven’t lived in a residence hall you’ll be pleased to know was shared with everyone on my floor (some 20 other young men).

I practiced with the new toy about three or four times before I let my partner do the deed. Each time I practiced I felt myself getting more excited about my big day, and I started to think about how much of an anal slut I truly was. Finally, the time had come. They came over during the day between classes and I spent the hour beforehand getting ready with enemas and stretching myself out. Having someone else control everything is such a different sensation. You feel more vulnerable but also hyper-aware of your body, which is very different when you’re on top.

When they arrived we started talking for a little while, but we were so excited that we jumped right into making out. Now, this is where things get a little funny. This was the first time this person and I had ever had sex, and the first time we ever kissed. God, they were the roughest kisser ever. Like, teeth pressing against my lips bad. Overall, a 4/10 on my kissing scale. Luckily, the ass fucking was a 9/10 at the time.

After making out and getting the initial formalities out of the way, they had me completely naked on top of a towel I laid out in case of any “accidents,” which at the time was my biggest fear out of anal sex. Now, they’re putting on their homemade harness (which was cleverly built out of straps) and weaved the strap-on I bought into the opening.

By now, I’m really nervous, lying on my back and waiting for the toy to plunge into me. But they started to speak calmly and reassured me as to how slowly they would start off. I nodded and let them press against my asshole until it greedily took in and swallowed half the length before they slowly pulled out and went back in.

What continued was slow thrusting and constant communication about if I needed more lube and if I wanted to go faster or slower. After 10 minutes I couldn’t take it anymore and began to stroke my cock while they picked up speed and fucked me hard as I stroked myself off. Finally, I yell out that I’m cumming and finish on my chest, and they lay down on top of me despite the sticky mess.

And that was the first time I had someone fuck my ass. It was pretty great. If you’re ever going to be someone’s first, remember: communication and lube. Those will make any anal experience so much more relaxing and enjoyable.

What was your first time being pegged like? I'd love to hear your stories! Let me know in the comments below!

Five years, more than 700 blogs, 50 videos, 40 podcasts, 3 events, 2 ebooks and 1 directory - LTASEX is a self-funded labor of love. If you get value out of LTASEX, consider tossing a couple bucks this way. Your donations help ease the burden on my slender pockets and allow me to spend more time working on new content for you.

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Five years, more than 700 blogs, 50 videos, 40 podcasts, 3 events, 2 ebooks and 1 directory - LTASEX is a self-funded labor of love. If you get value out of LTASEX, consider tossing a couple bucks this way. Your donations help ease the burden on my slender pockets and allow me to spend more time working on new content for you.